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Family-friendly vacation rentals in Greenwood Lake

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Greenwood Lake

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

An outdoor area features a spacious in-ground swimming pool surrounded by a well-maintained lawn. Comfortable lounge chairs are positioned nearby, offering a relaxing space in the shade of lush greenery. Tall trees provide privacy and a natural feel to the setting.

Home in New Paltz

4.98 out of 5 average rating, 496 reviews

midcentury mod * POOL * walk out trail to mohonk

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village Several outdoor seating areas. THE WHOLE PLACE IS YOURS FULL PRIVATE ACCESS HOUSE, POOL & PROPERTY POOL OPEN 5/1 - 9/30

Top guest favorite

The lakehouse is nestled among tall trees, with a spacious deck overlooking the water. Colorful flowers enhance the natural landscape, while a rocky shoreline leads to tranquil waters. Sunlight filters through the trees, creating dappled patterns on the house and surroundings.

Cottage in Highland Lake

4.97 out of 5 average rating, 334 reviews

The Mountaintop Lakehouse that Time Forgot.

Quiet Private lakehouse set down on 2 rare rock bluffs giving you a majestic water view just like it was in 1939. Extra Lg Great room w a huge fireplace. The great kitchen surrounds the chef. Big hot tub, Rowboat with canopy, 8 kayaks, Treehouse, Neverending Lakeside windows, docks, 1 hr from Manhattan w Eagles & vast wildlife like you were in the deep woods. Clean, unspoiled lake full of fish. Never had gas motors. A Mountaintop lake above the ski area. Stargazing! Perfect for get-togethers.

Top guest favorite

A serene view of Greenwood Lake is presented, showing calm waters reflecting the blue sky above. Moored boats line the shore, surrounded by lush greenery and distant hills, creating a peaceful lakeside atmosphere.

Home in Greenwood Lake

4.92 out of 5 average rating, 131 reviews

Casa del Lago, Boating, Hiking & Grilling!

Welcome to GWL! This 109 year old Arts & Crafts home is charming with high ceilings & beams, trim moldings, porch and original hardwood floors. There is plenty of outdoor space including back yard, a deck, patio & lake deck. Plenty of nooks for you to relax, grill, sip wine from the enclosed porch or watch TV. House faces the lake but you must cross a low traffic street for lake / dock access. Plenty of parking driveway & lakefront. Short walk to the Village, close to all! PERMIT #18-07697

A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.

Cabin in Sterling Forest

4.96 out of 5 average rating, 433 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

A cozy bedroom features a spacious bed adorned with decorative pillows. Wood paneling and a macramé wall hanging create a warm ambiance. Soft curtains frame the entrance, while two bedside lamps provide gentle lighting. A comfortable chair sits nearby on wood flooring.

Cottage in Highland Lake

4.94 out of 5 average rating, 193 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Cozy lake view cottage 50 miles from NYC. Nestled in nature with swimming, fishing , hiking and biking with beautiful lake views. 5 beaches to choose from. Lovely walking or jogging around the lake, Appalachian trail nearby. Highland Lakes is a very scenic, peaceful area easily accessible. 3 of the best golf courses in the US , Mountain Creek water park and resort minutes away.Apple and pumpkin picking comes fall. Beautiful village of Warwick NY is nearby with restaurants and shopping .

Top guest favorite

A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.

Cabin in Red Hook

4.96 out of 5 average rating, 358 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open May - October. During the colder months we recommend soaking in our giant freestanding tub, which easily fits two humans.] Welcome to Maitopia - our modern, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub for two, a floating fireplace for cozy winter moments and a heated pool. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Top guest favorite

A tiny house adorned with colorful outdoor lights stands against a night sky. Trees frame the property, while a bright moon casts a soft glow, adding to the serene atmosphere of the setting.

Tiny home in New Paltz

4.99 out of 5 average rating, 831 reviews

Hudson Valley Tiny House

If you've been looking for the tiny house experience, look no further. Michelle and Chris built this tiny house to live as eco-friendly, comfy, and healthy as possible. Built with only non-toxic and all natural materials with a state of the art fresh-air system. Enjoy wildlife or relaxing at the river bend on our 5-acre property or explore the awesome attractions close by: county pool, winery, New Paltz downtown, “gunks” rock climbing, Minnewaska State Park, and more!

The living room features two comfortable white sofas adorned with red accent pillows, positioned around a wooden coffee table. Natural light floods in through multiple windows, illuminating the space. A decorative flower arrangement sits on the table, enhancing the cozy ambiance.

Cottage in New Paltz

4.99 out of 5 average rating, 559 reviews

Stone House 1807. Comfort, Peace and Nature.

Historic 200 yr old stone cottage, on three floors, renovated to a high standard, creating a very comfortable and peaceful retreat, whilst retaining soul and character. Extreme cleanliness is a priority. Quality bedding assures a good nights sleep. The bathroom offers a rain shower and soaking tub. The kitchen is fully equipped and fresh produce is available from the neighboring organic farm in season. Good hiking trails are accessible from the house.

The exterior of a serene, handcrafted Japanese folk house is depicted, featuring wooden eaves and a unique slatted window design. Stacked firewood rests on the ground, surrounded by natural landscaping and tall trees, under a clear blue sky.

4.96 out of 5 average rating, 141 reviews

Little Minka - Japanese House in the Woods

Little Minka. A serene Japanese folk house nestled on 10 acres of private woodland and streams. Embracing the Wabi-Sabi, Little Minka is unique, handcrafted using Japanese traditional carpentry joinery methods. Soaring ceilings, shoji, and tatami complete the interior. Outside there's a fire pit, open cooking area. We have a wood fired hot tub on request. We have Japanese bathroom products in partnership with sowakanyc that guests can experience.

The exterior of the house is framed by lush greenery, including a prominent tree and colorful garden blooms. A gravel driveway leads to the entrance, which is partially visible on the right. The sky is tinged with soft sunset hues, lending a serene atmosphere.

Guest suite in Warwick

4.89 out of 5 average rating, 584 reviews

<The Painted House> Local Hiking/Garden views/Golf

<The Painted House> The house is on a 1 acre lot with a magnificent and magical perennial garden. I love decorating the space with my fun and eclectic finds. Warwick Permit #34239 Please feel free to inquire if you are traveling with more than 4 guests. Check out my Neighboring listings for more unique stays in Warwick, NY ! -Rabbit hill Cabin -3bedrooms Airbnb.com/h/rabbithillcabin -Pisces Pond Cabin-2bedrooms Airbnb.com/h/piscespondcabin

Top guest favorite

The farmhouse features a spacious front porch with several seating areas and a central entry door. The light-colored exterior is complemented by white trim and sizeable windows. Landscaping includes plant beds with yellow flowers and a decorative rooster statue on the side.

Farm stay in Goshen

4.87 out of 5 average rating, 359 reviews

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

Natural light floods a living area through large glass doors, which provide views of the garden and mountains. A comfortable couch faces a wooden coffee table, and a fireplace is situated beside a bookshelf filled with books. Decorative art enhances the space.

Chalet in Cold Spring

4.9 out of 5 average rating, 457 reviews

Mountain View Retreat

15 Minutes drive from Cold Spring & Beacon. 1 hour, 15 min by train or car from NYC. High-speed internet (wifi cell), cable, central AC, fireplace, large deck, mountain views, portable fire pit, gas grill and a 8 person hot tub. Featured in TIME OUT, "Best Airbnb Hudson Valley Rentals" Price change after 8 guests. Add guest number when booking, you can adjust it after booking. Specify beds you will need.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Greenwood Lake family-friendly rentals

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A bright living area features large windows that allow natural light to illuminate a pink sectional sofa adorned with colorful cushions. A white coffee table sits atop a light wooden floor, complemented by a decorative rug. Art pieces in warm hues are displayed on the wall.

Home in Olivebridge

4.92 out of 5 average rating, 458 reviews

Mountain-Top Catskills Getaway Cabin w/hot tub

An inviting living space showcases expansive floor-to-ceiling windows, allowing natural light to illuminate the room. A cozy sofa is complemented by stylish chairs, while a large area rug unifies the seating arrangement. Dining space is visible in the background, enhancing the open floor plan.

Cabin in Bethel

4.83 out of 5 average rating, 204 reviews

Stunning Mountain Cabin w/ Pool & Hot Tub

Home in Bushkill

4.83 out of 5 average rating, 130 reviews

Lakefront, Sale July 15-19, Pool, Hot Tub, Arcade

The exterior of the Equestrian Suite is showcased, featuring a two-story structure with a blend of brick and wood. A wrap-around balcony offers scenic views, and lush greenery surrounds the property, complementing the tranquil mountain setting.

Guesthouse in Beacon

4.94 out of 5 average rating, 400 reviews

Cozy Mountainside Suite - Minutes from Beacon

The exterior of the guest house is shown alongside a wooden chicken coop. The house features large windows and a red roof. Lush green grass surrounds the area, with hints of autumn foliage visible on nearby trees.

Guesthouse in Forestburgh

4.97 out of 5 average rating, 425 reviews

Guesthouse On 1879 Farm. Hot tub and hiking

An aerial view captures a charming cabin surrounded by lush trees, with a vibrant sunset sky in shades of pink and purple. The spacious yard is highlighted by a hot tub, outdoor seating area, and fire pit, inviting relaxation and gatherings in nature.

Cabin in Livingston Manor

4.97 out of 5 average rating, 309 reviews

Experience The Zen House

Top guest favorite

The interior of the cabin features wooden beams and a high ceiling, creating an open atmosphere. A cozy seating area includes a rustic coffee table and a propane gas fireplace. The kitchen and dining area are visible in the background, showcasing wooden cabinets and a large dining table.

Cabin in Cochecton

5 out of 5 average rating, 135 reviews

Log Cabin * Hot Tub * Sauna * 4.6 mi. Bethel Woods

A spacious living area is furnished with a large sectional sofa, adorned with decorative throw pillows. Natural light filters through multiple tall windows, illuminating a central coffee table accompanied by simple decor. In the background, a large dining table and green accents enhance the inviting atmosphere.

Home in High Falls

4.95 out of 5 average rating, 220 reviews

Clove Schoolhouse on Mohonk Preserve

Family- and pet-friendly home rentals

An exterior view of an old milk barn, featuring a wooden door and overgrown greenery surrounding the structure. The rustic charm is highlighted by exposed brick and an angled roof. A few outdoor furniture pieces are positioned nearby, complementing the natural setting.

Farm stay in High Falls

4.87 out of 5 average rating, 954 reviews

Dave's Milk Barn

The exterior of a country home is framed by lush trees, with an American flag gently waving from the porch. Flower containers add color along the stone pathway leading to the steps, which provide access to a screened-in area overlooking the river.

Home in Damascus

4.95 out of 5 average rating, 179 reviews

Delaware River retreat

Top guest favorite

The interior features exposed wooden beams and walls, with a warm wooden floor. A cozy living area accommodates a dark sofa and a fireplace. A dining table with four chairs is positioned nearby, and large glass doors provide access to outdoor views.

Cabin in Boiceville

4.98 out of 5 average rating, 516 reviews

Winston's Place - Woodland Cozy Catskills Cabin

Top guest favorite

A charming wooden exterior characterizes the home, complemented by a red roof and flower-filled window boxes. Lush greenery surrounds the property, and decorative sheep figures line the fence. A small patio area with pavement is visible, leading to the entrance of the house.

Home in New Paltz

4.97 out of 5 average rating, 759 reviews

Victorian Haven

Top guest favorite

Home in Callicoon

4.99 out of 5 average rating, 314 reviews

Paradise in the Catskills

Top guest favorite

A vintage Airstream camper is nestled among vibrant autumn foliage, featuring shades of red and yellow. Surrounding the camper are rugged stones and a rustic outdoor seating area. The ground is covered in fallen leaves, enhancing the natural ambiance of the wooded setting.

Camper/RV in Cold Spring

4.95 out of 5 average rating, 534 reviews

Hudson Highlands Base Camp

A spacious living area features large windows allowing ample natural light, surrounded by greenery. Comfortable seating arrangements include a blue sofa and armchairs with red accents. A patterned area rug anchors the space, complemented by a wooden coffee table and decorative wall elements.

Home in Livingston Manor

4.96 out of 5 average rating, 232 reviews

Wooded Livingston Manor Oasis With Stream & Deck

A sweeping view of the Hudson River framed by vibrant autumn foliage. The landscape showcases a mix of red, orange, and yellow trees with hills in the background, creating a tranquil natural setting. Mist softly blankets the distant mountains.

Guest suite in Fort Montgomery

4.94 out of 5 average rating, 467 reviews

West Point - Mountain Top Suite

Family-friendly home rentals with a pool

A spacious living area features a large sectional sofa and a fluffy area rug. Natural light floods the room, highlighting the hardwood floors. An open kitchen with modern appliances is visible in the background, while a dining area is located near the staircase.

Home in Woodstock

4.88 out of 5 average rating, 168 reviews

Shula | Farmhouse | Pool, Fire pit, Hot tub

An aerial view showcases a spacious home surrounded by lush greenery, featuring a 33-foot round swimming pool in the backyard. The inviting pool is surrounded by a deck, with lounge chairs positioned nearby, providing a serene outdoor setting.

Home in Tobyhanna

4.8 out of 5 average rating, 130 reviews

Cozy home for 10 ~ Private pool, BBQ, fire pit

The exterior of The Appalachian Lodge is displayed, showcasing a multi-story building with a combination of warm colors and architectural details. A heated outdoor pool and lounging area are visible in the foreground, surrounded by landscaped grounds and comfortable seating options.

Condo in Vernon Township

4.94 out of 5 average rating, 854 reviews

Appalachian Lodge Top Floor w/views

A wooden dock extends into the lake, featuring a welcoming bench for relaxation. Adirondack chairs are placed nearby, with vibrant greenery surrounding the area. A boat is visible at the side, and the lake provides a serene backdrop to the renovated home in the distance.

Home in Tobyhanna

4.9 out of 5 average rating, 217 reviews

#1 Lakefront Hot Tub, Pool, Boat, Fire Pit, Casino

A charming cottage entrance features a distinctive blue garage door adorned with colorful accents. Two chairs are positioned beside vibrant flower arrangements, inviting relaxation. The building is framed by lush greenery and tall trees, enhancing its cozy and welcoming appearance.

Cottage in West Orange

4.87 out of 5 average rating, 207 reviews

Cozy Pool Cottage

An aerial view captures the serene landscape surrounding the cottage, featuring a bright blue pool bordered by a wooden deck. Lush greenery envelops the area, with trees providing shade and a sense of seclusion, while the cottage sits nestled in the background.

Cottage in Woodstock

4.81 out of 5 average rating, 118 reviews

Woodstock Mountain Cottage w/ Pool

A saltwater pool is surrounded by a stone patio, with lush greenery and wildflowers near the edges. The serene water reflects the soft colors of the sunset, and the distant mountains are visible in the background, creating a peaceful setting.

Cottage in West Hurley

4.94 out of 5 average rating, 268 reviews

Woodstock Carriage House HotTub FirePit Pool

A charming carriage house features large windows and a high peaked roof, set amidst lush greenery. A well-maintained pool with a gentle fountain is situated in front, surrounded by landscaped gardens and inviting white lounge chairs.

Home in Englewood

4.92 out of 5 average rating, 160 reviews

Englewood NJ Country Carriage House (15 min NYC)

Quick stats about vacation rentals that are family-friendly in Greenwood Lake

Total rentals
40 properties
Nightly prices starting at
€ 120 before taxes and fees
Total number of reviews
3.4K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
40 properties include access to wifi

Destinations to explore